CN1578556A - Organic electroluminescent device - Google Patents
Organic electroluminescent device Download PDFInfo
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- CN1578556A CN1578556A CNA2004100600740A CN200410060074A CN1578556A CN 1578556 A CN1578556 A CN 1578556A CN A2004100600740 A CNA2004100600740 A CN A2004100600740A CN 200410060074 A CN200410060074 A CN 200410060074A CN 1578556 A CN1578556 A CN 1578556A
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- 125000004429 atom Chemical group 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
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- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
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- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000005581 pyrene group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- JUJWROOIHBZHMG-RALIUCGRSA-N pyridine-d5 Chemical compound [2H]C1=NC([2H])=C([2H])C([2H])=C1[2H] JUJWROOIHBZHMG-RALIUCGRSA-N 0.000 description 1
- 150000003921 pyrrolotriazines Chemical class 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- PEQHIRFAKIASBK-UHFFFAOYSA-N tetraphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 PEQHIRFAKIASBK-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000005259 triarylamine group Chemical class 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- MEYZYGMYMLNUHJ-UHFFFAOYSA-N tunicamycin Natural products CC(C)CCCCCCCCCC=CC(=O)NC1C(O)C(O)C(CC(O)C2OC(C(O)C2O)N3C=CC(=O)NC3=O)OC1OC4OC(CO)C(O)C(O)C4NC(=O)C MEYZYGMYMLNUHJ-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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Abstract
Provided is an organic electroluminescent device having a high-efficiency optical output with high luminance and long life, which includes at least: a pair of electrodes comprising an anode and a cathode; and one or more organic-compound-containing layers sandwiched between the pair of electrodes, and in which among the organic-compound-containing layers, at least one layer having a light-emitting region contains a first compound represented by the following general formula [1] and a second compound having a band gap larger than a band gap of the first compound.
Description
Technical field
The present invention relates to adopt the light-emitting component of organic compound, relate in more detail by on the film that forms by organic compound, applying the organic illuminating element that electric field sends light.
Background technology
The film that comprises the fluorescence organic compound in organic illuminating element clamping between anode and negative electrode, by inject electronics or hole (positive hole) from each electrode, generate the exciton of fluorescence compound, this exciton is launched light when turning back to ground state, and the light that organic illuminating element has just utilized this to launch.
In the research (non-patent literature 1) of コ ダ ッ Network society in 1987, disclosing a kind of anode adopts ITO, negative electrode to adopt the element of 2 layers of structure of function divergence type of magnesium silver alloy, wherein adopt aluminium oxyquinoline ligand as electron transport materials and luminescent material, adopt triphenylamine derivative as hole transporting material, applying under the voltage about 10V, send 1000cd/m
2The light of size.As relevant patent, can enumerate patent documentation 1～3 etc.
In addition,, can send from ultraviolet, also carry out the research of all cpds recently actively to infrared light by changing the kind of fluorescence organic compound.For example, just on the books in patent documentation 4～11 grades.
In addition, except the organic illuminating element as the low molecular material of above-mentioned employing, the research group of Cambridge University (non-patent literature 2) also discloses the high molecular organic illuminating element of employing conjugated type.In this report, confirmed by making polyphenylene vinylene (PPV) film forming with the coating system, can individual layer luminous.As with adopt the relevant patent of the high molecular organic illuminating element of conjugated type, can enumerate patent documentation 12～16 etc.
Significantly progressive recently aspect this organic illuminating element, since it is characterized by low applying can have high briliancy, emission wavelength diversity, high-speed response under the voltage and luminescent device slim, light weight is changed into be possible, therefore demonstrate its availability in extensive use.
But,, or, also have more problem because to comprise the atmosphere gas of oxygen and moisture etc. former thereby become of inferior quality durability aspect and be not resolved as yet because to use the back to take place aging long-time.In addition, considering to be applied under the situation of full-color display etc., its present situation is a light that must the higher briliancy of output or luminous expeditiously.
As the example of material that comprises anthracene nucleus and organic illuminating element, a kind of benzene anthracene derivant is disclosed in patent documentation 17.Particularly, can form good organic membrane because its crystallinity is low, but its luminous efficiency and durability also are not enough to reach practical application adopting it to inject under the situation of carrying material as cyan luminescent material and electronics.
As other examples, amino anthracene derivative and diaminoanthraquinone-derivative are disclosed respectively in patent documentation 18, patent documentation 19.Can send green light when adopting it, but the luminous efficiency of element is low, and also is not enough to reach practical application about its durability as luminescent material.
As other examples, in patent documentation 20, disclose and adopted the element of specific two anthryl compounds, thereby can obtain the luminous of high briliancy as luminescent material, but for luminous efficiency and not record of durability.
As other examples, in patent documentation 21, disclose employing and comprised the element of the specific anthracene compound at alkene position, thereby can send the light from the yellow to the redness, but its luminous efficiency also is not enough to reach practical application as luminescent material.
As other examples, the element that comprises anthracene derivant, electron transport compound and other fluorescence compounds of ad hoc structure at the luminescence medium layer is disclosed in patent documentation 22.Although can obtain the red light-emitting component that reliability has been improved, its luminous efficiency also is not enough to reach practical application, and also be difficult to obtain the luminous of cyan on component structure.
No. 4539507 specification of patent documentation 1 United States Patent (USP)
No. 4720432 specification of patent documentation 2 United States Patent (USP)s
No. 4885211 specification of patent documentation 3 United States Patent (USP)s
No. 5151629 specification of patent documentation 4 United States Patent (USP)s
No. 5409783 specification of patent documentation 5 United States Patent (USP)s
No. 5382477 specification of patent documentation 6 United States Patent (USP)s
Patent documentation 7 spies open flat 2-247278 communique
Patent documentation 8 spies open flat 3-255190 communique
Patent documentation 9 spies open flat 5-202356 communique
Patent documentation 10 spies open flat 9-202878 communique
Patent documentation 11 spies open flat 9-227576 communique
No. 5247190 specification of patent documentation 12 United States Patent (USP)s
No. 5514878 specification of patent documentation 13 United States Patent (USP)s
No. 5672678 specification of patent documentation 14 United States Patent (USP)s
Patent documentation 15 spies open flat 4-145192 communique
Patent documentation 16 spies open flat 5-247460 communique
Patent documentation 17 spies open flat 8-12600 communique
Patent documentation 18 spies open flat 9-157643 communique
Patent documentation 19 spies open flat 10-72579 communique
No. the 3008897th, patent documentation 20 Japan Patents
Patent documentation 21 spies open flat 11-8068 communique
Patent documentation 22 spies open the 2001-284050 communique
Non-patent literature 1 Appl.Phys.Lett.51,913 (1987)
Non-patent literature 2 Nature, 347,539 (1990)
Summary of the invention
The purpose of this invention is to provide a kind of organic illuminating element with high efficiency, high briliancy, the output of long-life light.
Present inventors etc. have carried out wholwe-hearted research for addressing the above problem, and have finally finished the present invention.
That is, organic illuminating element of the present invention has 1 pair of electrode that anode and negative electrode form at least, and clamping between this 1 pair of electrode comprises the layer of a kind or multiple organic compound,
In comprising the layer of described organic compound, at least 1 layer of light-emitting zone contains the 1st compound shown in the following general formula [1] and has 2nd compound wideer than the 1st compound band gap.
(in general formula [1], A represents to comprise the molecular cell of aromatic rings, fused polycycle, heterocycle etc.
Y
1, Y
2For being selected from replacement or unsubstituted alkyl, aralkyl, aryl and heterocyclic radical, having the group that connects basic divalent substituent, the two can be the same or different.Perhaps, Y
1, Y
2Also can interosculate and form ring.Perhaps, the Y on different anthracene deriveding groups
1And Y
2Can be the same or different.
Z
1Be the heterocyclic radical that is selected from direct key, replacement or unsubstituted arlydene and divalence, the group with the divalent substituent that is connected base, it can be the same or different.Z
2And Z
3For being selected from direct key, replacement or unsubstituted alkylidene, alkenylene, alkynylene, arylmethylene alkyl, arylene and divalent heterocycle, having the group that is connected basic divalent substituent, it can be the same or different.
X
1Be silicyl, the boryl that is selected from hydrogen atom, D atom, halogen atom, replacement or unsubstituted alkyl, thiazolinyl, alkynyl, aralkyl, alkoxyl and sulfenyl, aryl and heterocyclic radical, replacement, the group with the divalent substituent that is connected base, it can be the same or different.X
2For be selected from replace or unsubstituted aryl with heterocyclic radical, have the group that is connected basic divalent substituent, it can be the same or different.
R
1And R
2For being selected from the group of hydrogen atom, D atom, halogen atom, replacement or unsubstituted alkyl, aryl, alkoxyl, amino, it can be the same or different.R
3For being selected from the group of hydrogen atom, D atom, halogen atom, replacement or unsubstituted alkyl, alkoxyl, it can be the same or different.
A is 0～6 integer.b+c+d＝6-a。But when a+b is a integer more than 2, during a=0, the X on anthryl
1In, have at least one to comprise hydrogen atom, D atom, halogen atom substituting group in addition.)
In addition, described the 1st compound of organic illuminating element of the present invention such as following general formula [2] expression.
(in general formula (2), Y
3, Y
4For being selected from replacement or unsubstituted alkyl, aralkyl, aryl and heterocyclic radical, having the group that is connected basic divalent substituent, it can be the same or different.In addition, Y
3, Y
4Also can be connected to each other and form ring.In addition, the different anthracenes Y on the base that derives
3, Y
4Can be the same or different.
Z
4Be the heterocyclic radical that is selected from direct key, replacement or unsubstituted arlydene and divalence, the group with the divalent substituent that is connected base, it can be the same or different.Z
5And Z
6For be selected from direct key, replacement or unsubstituted alkylidene, alkenylene, alkynylene, inferior aralkyl, arylene with divalent heterocycle, have the group of divalent substituent that is connected base, it can be the same or different.
X
3Be silicyl, the boryl that is selected from hydrogen atom, D atom, halogen atom, replacement or unsubstituted alkyl, thiazolinyl, alkynyl, aralkyl, alkoxyl and sulfenyl, aryl and heterocyclic radical, replacement, the group with the divalent substituent that is connected base, it can be the same or different.X
4For be selected from replace or unsubstituted aryl with heterocyclic radical, have the group that is connected basic divalent substituent, it can be the same or different.
R
4And R
5For being selected from the group of hydrogen atom, D atom, halogen atom, replacement or unsubstituted alkyl, aryl, alkoxyl, amino, it can be the same or different.R
6For being selected from the group of hydrogen atom, D atom, halogen atom, replacement or unsubstituted alkyl, alkoxyl, it can be the same or different.
E is 0～6 integer.f+g+h＝6-e。But when e+f is a integer more than 2, during e=0, the X on anthryl
3In, have at least one to comprise hydrogen atom, D atom, halogen atom substituting group in addition.)
In addition, the HOMO energy level of above-mentioned the 1st compound is than the energy level height of the 2nd compound, and the lumo energy of above-mentioned the 1st compound is lower than the lumo energy of the 2nd compound.
In addition, above-mentioned the 2nd compound is shown in following general formula [3].
(in general formula [3], R
7, R
8, R
9And R
10Amino, cyano group or the halogen atom of expression hydrogen atom, replacement or unsubstituted alkyl, replacement or unsubstituted aralkyl, replacement or unsubstituted aryl, replacement or unsubstituted heterocyclic, replacement.R
7, R
8, R
9And R
10Can be identical, also can be different.Ar
1And Ar
2Expression replaces or unsubstituted condensed polycyclc aromatic base or expression replacement or unsubstituted fused polycycle heterocyclic radical, Ar
1And Ar
2Can be identical, also can be different.)
In addition, above-mentioned the 2nd compound such as following general formula [4] expression.
(in general formula [4], R
11And R
12Amino, cyano group or the halogen atom of expression hydrogen atom, replacement or unsubstituted alkyl, replacement or unsubstituted aralkyl, replacement or unsubstituted aryl, replacement or unsubstituted heterocyclic, replacement.R
11And R
12Can be identical, also can be different.R
13And R
14Expression hydrogen atom, replacement or unsubstituted alkyl, replacement or unsubstituted aralkyl, replacement or unsubstituted aryl or replacement or unsubstituted heterocyclic.R
13And R
14Can be identical, also can be different.Ar
3And Ar
4The expression phenyl ring is replacement or the unsubstituted condensed polycyclc aromatic base more than 3 or represents that phenyl ring is replacement or the unsubstituted fused polycycle heterocyclic radical more than 3, Ar
3And Ar
4Can be identical, also can be different.N represents 1～10 integer.)
Brief description of drawings
Fig. 1 is the sectional view of an example of demonstration organic illuminating element of the present invention.
Fig. 2 is the sectional view of an example of demonstration organic illuminating element of the present invention.
Fig. 3 is the sectional view of an example of demonstration organic illuminating element of the present invention.
Fig. 4 is the sectional view of an example of demonstration organic illuminating element of the present invention.
Fig. 5 is the sectional view of an example of demonstration organic illuminating element of the present invention.
Fig. 6 is the schematic diagram that is used for illustrating the HOMO/LUMO energy level preference relation of light-emitting component light-emitting zone the 1st compound of the present invention and the 2nd compound.
Embodiment
Below the present invention is described in detail.
Fig. 1 constitutes the ideograph of example for expression organic illuminating element of the present invention to Fig. 5.
Symbol appended in each figure is represented respectively
1 substrate
2 anodes
3 luminescent layers
4 negative electrodes
5 hole transporting layers
6 electron supplying layers
7 hole injection layers
8 holes/exciton-blocking layers
Fig. 1 is provided with anode 2, luminescent layer 3 and negative electrode 4 in order and constitutes on substrate 1.When luminescent layer himself single be useful when having cavity conveying energy, electron transport energy and luminiferous performance.
Fig. 2 is provided with anode 2, hole transporting layer 5, electron supplying layer 6 and negative electrode 4 in order and constitutes on substrate 1.At this moment, light-emitting zone is any one deck in hole transporting layer 5 and the electron supplying layer 6.By the function of cavity conveying and electron transport being assigned in the different layers, can increase the degree of freedom of selecting material, and can improve performance.
Fig. 3 is provided with anode 2, hole transporting layer 5, luminescent layer 3, electron supplying layer 6 and negative electrode 4 in order and constitutes on substrate 1.In this case, carrier transport is separated with lighting function, the compound that has cavity conveying, electron transport, luminiferous various characteristics by employing also suitably makes up, not only greatly increased the degree of freedom of selecting material, simultaneously the different all cpds of emission wavelength can be used, therefore luminous form and aspect variation can be made.In addition, in the luminescent layer 3 of central authorities, various charge carriers or exciton can be sealed effectively, therefore also luminous efficiency can be improved.
Fig. 4 inserts hole injection layer 7 with respect to Fig. 3 in anode 2 sides and constitutes.It has the connecting airtight property of improving anode 2 and hole transporting layer 5 or the effect of improving the hole injection, and the effect that obtains low-voltage.
Fig. 5 inserts between luminescent layer 3-electron supplying layer 6 with respect to Fig. 3 to stop the layer (hole blocking layer 9) that hole or exciton overflow in negative electrode 4 sides and constitute.By adopting the bigger compound of ionization potential, can obtain to improve the effect of luminous efficiency as hole blocking layer 9.
Feature of the present invention is to comprise the 1st compound shown in the formula [1] and have 2nd compound wideer than the 1st compound band gap in the light-emitting zone that element constitutes as mentioned above, and the main light that sends from the 1st compound that utilizes.
Particularly preferably be and select compound respectively, so that the absorbing wavelength scope of the absorbing wavelength scope of the 1st compound and the 2nd compound is overlapping, can promote that thus carrying out energy from the 2nd compound to the 1st high compound of luminous efficiency moves, thereby can improve the luminous efficiency of element.
On the contrary, when the band gap of the 2nd compound was narrower, effectively the 1st compound that utilization ratio is high was luminous.
In addition, compare, as adopting the two advantage of the 1st compound and the 2nd compound to enumerate with the situation that adopts the 1st compound monomer
(1) by joining the inhibition concentration delustring with the 1st compound
(2) by with the 2nd compound, improve film forming
(3) by adopting 2 kinds of compounds, the carrier balance in electron gain and hole etc. easily can obtain luminous expeditiously and improves the effect in life-span.For obtaining aforesaid effect, the 1st compound concentrations is 0.01%～80% in the preferred light-emitting zone, in particular for the effect that obtains above-mentioned (1)～(3) and obtain good balance, is preferably 1～40%.
The concentration of mixing can be impartial in light-emitting zone, also can have concentration gradient.
In addition, for strengthening above-mentioned effect, can further add the 3rd compound.In this case, it is also important that selection the 3rd compound is wideer than the band gap of the 1st compound.Band gap can be obtained by measuring uv-visible absorption spectroscopy.
The feature of the 1st compound of general formula [1] and [2] expression is at least 2 above anthryls that cooperate on aromatic rings, fused polycycle or heterocycle core as luminescence unit, and further on each anthryl, be substituted with amino, have the basic amino of connection, aryl etc., can obtain high efficiency luminous.In addition, particularly by change anthryl and amino substituting group, the adjustable light color of haircuting sends from the cyan to the green it, even the light of long wavelength side color more.
By importing substituted-amino, also can further improve the cavity conveying energy.By on anthryl, carrying out the replacement of amino etc., can improve Tg (exemplary compounds 34 for example shown below Tg=215 ℃), by forming an array of stars type dendrimer shape, can obtain the material of film forming and good thermal stability.
Above-mentioned general formula [1] is as follows with the instantiation that is connected base, substituting group and molecular cell A in [2].
In above-mentioned general formula [1] and [2], as connecting base, can enumerate and replace or the heterocyclic radical of unsubstituted arlydene or divalence etc., but certain be that it is not limited to these groups.
In above-mentioned general formula [1] and [2], as having the divalent substituent that connects base, can enumerate and replace or the silicyl of unsubstituted alkylidene, alkenylene, alkynylene, arylmethylene alkyl and amino, replacement, ether, thioether group, carbonyl etc., but certain be that it is not limited to these groups.
As replacing or unsubstituted alkyl, can enumerate methyl, methyl-d1 base, methyl-d3 base, ethyl, ethyl-d5 base, n-pro-pyl, normal-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, positive decyl, isopropyl, isopropyl-d7 base, isobutyl group, sec-butyl, the tert-butyl group, the tert-butyl group-d9 base, sec-amyl, neopentyl, uncle's octyl group, the fluoro methyl, two fluoro methyl, three fluoro methyl, 2-fluoro ethyl, 2,2,2-three fluoro ethyls, the perfluoro ethyl, 3-fluoro propyl group, the perfluoro propyl group, 4-fluoro butyl, the perfluoro butyl, 5-fluoro amyl group, 6-fluoro hexyl, the chloro methyl, three chloro methyl, 2-chloro ethyl, 2,2,2-three chloro ethyls, 4-chloro butyl, 5-chloro amyl group, 6-chloro hexyl, bromomethyl, the 2-bromoethyl, iodo-methyl, 2-iodo ethyl, hydroxymethyl, hydroxyethyl, cyclopropyl, cyclobutyl, cyclopenta, cyclohexyl, cyclopentyl-methyl, cyclohexyl methyl, the cyclohexyl ethyl, 4-fluoro cyclohexyl, the norborneol alkyl, adamantyl etc., but certain be that it is not limited to these groups.
As replacing or unsubstituted aralkyl, can enumerate benzyl, 2-phenylethyl, 2-propyloxy phenyl base, 1-menaphthyl, 2-menaphthyl, 2-(1-naphthalene) ethyl, 2-(2-naphthalene) ethyl, 9-anthryl methyl, 2-(9-anthryl) ethyl, 2-fluoro benzyl, 3-fluoro benzyl, 4-fluoro benzyl, 2-chloro benzyl, 3-chloro benzyl, 4-chloro benzyl, 2-benzyl bromide, 3-benzyl bromide, 4-benzyl bromide etc., but certain be that it is not limited to these groups.
As replacing or unsubstituted thiazolinyl, can enumerate vinyl, pi-allyl (2-acrylic), 1-acrylic, isopropenyl, 1-cyclobutenyl, 2-cyclobutenyl, 3-cyclobutenyl, styryl etc., but certain be that it is not limited to these groups.
As replacing or unsubstituted alkynyl, can enumerate acetenyl, phenylacetylene base, 1-propinyl etc., but certain be that it is not limited to these groups.
As replacing or unsubstituted aryl, can enumerate phenyl, phenyl-d5 base, the 4-aminomethyl phenyl, the 4-methoxyphenyl, the 4-ethylphenyl, 4-fluoro phenyl, 4-trifluoro-benzene base, 3, the 5-3,5-dimethylphenyl, 2,6-diethyl phenyl, (mesityl) base, the 4-tert-butyl-phenyl, two (tolyl aminophenyls), xenyl, triphenyl, the 1-naphthyl, the 2-naphthyl, 1-naphthyl-d7 base, 2-naphthyl-d7 base, the 1-anthryl, the 2-anthryl, the 9-anthryl, 9-anthryl-d9 base, the 2-phenanthryl, the 3-phenanthryl, the 4-phenanthryl, the 9-phenanthryl, 9-phenanthryl-d9 base, the 1-pyrenyl, 1-pyrene-d9 base, the 2-pyrenyl, the 4-pyrenyl, the tetrad phenyl, the 5-linked phenyl, fluorenyl, triphenyl perylene base etc., but certain be that it is not limited to these groups.
As replacing or unsubstituted heterocyclic, can enumerate pyrrole radicals, pyridine radicals, pyridine-d5 base, bipyridyl, picolyl, tripyrrole base, thienyl, thiophene-d4 base, three thienyls, propyl group thienyl, furyl, furans-d4 base, indyl, 1,10-phenanthroline, phenanthridinyl, quinolyl, carbazyl, oxazolyl, oxadiazole base, thiazolyl, thiadiazolyl group etc., but certain be that it is not limited to these groups.
As replacing or unsubstituted alkylidene, can enumerate methylene, methylene-d2 base, two fluoro methylene, ethylidene, ethylidene-d4 base, perfluoro ethylidene, propylidene, isopropylidene, butylidene, 2,2-dimethyl propylidene etc., but certain be that it is not limited to these groups.
As replacing or unsubstituted arylmethylene alkyl, can enumerate benzal, 2-phenyl ethylidene, 2-phenyl isopropylidene, 1-naphthal, 2-naphthal, 9-anthryl methylene, 2-fluoro benzal, 3-fluoro benzal, 4-fluoro benzal, 4-chloro benzal, 4-bromo benzal etc., but certain be that it is not limited to these groups.
As replacing or unsubstituted alkenylene, can enumerate ethenylidene, different-allylidene, inferior styryl, 1,2-diphenyl ethenylidene etc., but certain be that it is not limited to these groups.
As replacing or unsubstituted alkynylene, can enumerate ethynylene, phenyl ethynylene etc., but certain be that it is not limited to these groups.
As replacing or unsubstituted arlydene, can enumerate phenylene, biphenylene, tetrafluoro for phenylene, dimethyl phenylene, naphthylene, anthrylene, phenanthrylene, inferior pyrenyl, inferior tetrad phenyl, inferior 5-linked phenyl, perylene base etc., but certain be that it is not limited to these groups.
As replacing or unsubstituted divalent heterocycle, can enumerate furylidene, inferior pyrrole radicals, inferior pyridine radicals, Sanya pyridine radicals, inferior thienyl, Sanya thienyl, Ya oxazolyl, inferior thiazolyl, inferior carbazyl etc., but certain be that it is not limited to these groups.
As replacing or unsubstituted amino (NR ' R "); R ' and R " can be hydrogen atom, D atom, replacement as implied above or unsubstituted alkyl, aralkyl, aryl, heterocyclic radical, have by replacing or the alkylidene of the connection base that unsubstituted arlydene or divalent heterocycle form, alkenylene, alkynylene, arylmethylene alkyl and amino, the silicyl that replaces, ether, thioether group, carbonyl, for example can enumerate amino, the N-methylamino, the N-ethylamino, N, the N-dimethylamino, N, the N-diethylamino, N-methyl-N-ethylamino, the N-benzylamino, N-methyl-N-benzylamino, N, the N-dibenzyl amino, anilino-, N, the N-diphenyl amino, N-phenyl-N-tolyl amino, N, N-xylyl amino, N-methyl-N-phenyl amino, N, N-dianisolylamino, N-base-N-phenyl amino, N, N-two bases are amino, N-phenyl-N-(4-tert-butyl-phenyl) amino, N-phenyl-N-(4-three fluoro aminomethyl phenyls) amino etc., but certain be that it is not limited to these groups.
As replacing or unsubstituted alkoxyl, can enumerate the aryloxy group of replacement with above record or unsubstituted alkyl, alkoxyl, the aralkoxy of aralkyl, replacement or unsubstituted aryl, heterocyclic radical with above record, for example can enumerate methoxyl group, ethyoxyl, propoxyl group, 2-ethyl-octyloxy, phenoxy group, 4-tert-butyl group phenoxy group, benzyl oxygen base, thiophene oxy etc., but certain be that it is not limited to these groups.
As replacing or unsubstituted sulfenyl, can enumerate replacement with above record or unsubstituted alkyl, alkylthio group, the aromatic alkylthio of aralkyl, replacement or unsubstituted aryl, the aryl of heterocyclic radical, the arylthio of heterocyclic radical with above record, for example can enumerate methyl mercapto, ethylmercapto group, thiophenyl, 4-aminomethyl phenyl sulfenyl etc., but certain be that it is not limited to these groups.
As molecular cell A, can enumerate the replacement or the unsubstituted phenyl ring that comprise heavy hydrogen, cyclohexyl biphenyl, three phenyl ring, naphthalene nucleus, Fei Nan Silin (phenanthrene) ring, anthracene nucleus, the aphthacene ring, the benzo anthracene nucleus, the ring, pyrene ring perylene ring, the corannulene ring, the Sanya phenyl ring, thiphene ring, pyridine ring, the pyrazine ring, the pyrazoles ring, pyrrole ring, three thiphene ring, three pyridine rings, the tripyrrole ring, triazole ring, the carbazole ring, the benzimidazole ring, the benzothiazole ring, quinoline ring quinoxalinyl, quinazolyl, the phthalazines ring, the diphenyl methane ring, tetraphenyl silane silane, the tetraphenyl germne, tetraphenylmethane etc., but certain be that it is not limited to these groups.
As above-mentioned substituting group, connect base, the substituting group that molecular cell A can further have, can enumerate D atom, methyl, ethyl, n-pro-pyl, normal-butyl, n-pentyl, n-hexyl, n-hexyl, n-heptyl, n-octyl, positive decyl, isopropyl, isobutyl group, sec-butyl, the tert-butyl group, isopentyl, neopentyl, uncle's octyl group, benzyl, the alkyl of 2-phenylethyl etc., aralkyl, methoxyl group, ethyoxyl, propoxyl group, 2-ethyl-octyl group oxygen base, phenoxy group, 4-tert-butyl group phenoxy group, the alkoxyl of benzyl oxygen base etc., phenyl, the 4-aminomethyl phenyl, the 4-ethylphenyl, the 3-chlorophenyl, 3, the 5-3,5-dimethylphenyl, triphenyl amino, xenyl, triphenyl, naphthyl, anthryl, phenanthryl, the aryl of pyrenyl etc., pyridine radicals, bipyridyl, picolyl, thienyl, three thienyls, the propyl group thienyl, furyl, quinolyl, carbazyl, the heterocyclic radical of N-ethyl carbazole base etc., halogen, hydroxyl, cyano group, nitro etc., but certain be that it is not limited to these groups.
For the compound of general formula [1] and [2] expression, can enumerate following typical example.
Further, as shown in Figure 6, the preferred compound of selecting like this make the HOMO energy level of the 1st compound than the HOMO energy level height of the 2nd compound, and the lumo energy of above-mentioned the 1st compound is lower than the lumo energy of the 2nd compound.
Thus, can increase electronics and hole and directly be combined in probability on the 1st compound once more, can improve the luminous efficiency of element.
The HOMO energy level of the 1st luminophor and the 2nd luminophor can be obtained by UPS (ultraviolet photoelectron optical spectroscopy) and other electronics beam split means (for example analyzer name be called the AC-1 reason grind the machine manufacturing), cyclic voltammetry oxidizing potential etc.Lumo energy can carry out Calculation Method by light absorption band gap measured value and above-mentioned HOMO energy level, is perhaps obtained by the cyclic voltammetry reduction potential.In addition, also can predict HOMO, lumo energy by the analog computation of electronic orbit method and density general purpose function method etc.
As the 2nd compound, the compound shown in preferred formula [3] and [4].Any compound all is to be the center with firm and fluffy unit, and have the condensed polycyclc aromatic base or a fused polycycle heterocyclic radical of charge transport characteristic and excellent in luminous characteristics, be difficult to take place crystallization etc. thus, thereby make the ageing stability excellence, and element can be luminous expeditiously.
Below exemplified the typical example of compound shown in the general formula [3].
Below exemplified the typical example of compound shown in the general formula [4].
The present invention relates to be present in the organic layer in the light-emitting zone, but other organic layer (hole injection layer, hole transporting layer, electron supplying layer etc.) can use known so far material as required.
These examples for compounds have below been exemplified.
Inject to carry material as the positivity hole, preferably carry out the hole from anode easily and inject maybe and injected holes can be delivered to material luminescent layer, that have excellent mobility.Inject the low molecule and the high score subclass material of transportation performance as having the positivity hole, can enumerate triarylamine derivative, phenylenediamine derivative, triazole derivative, oxadiazole derivative, imdazole derivatives, pyrazoline derivative, pyrazolone derivative, oxazole derivative, fluorenone derivatives, hydazone derivative, stilbene derivatives, phthalocyanine derivates, derivatives of porphyrin and poly-(vinyl carbazole), poly-(first silene), poly-(thiazole) and other electroconductive polymer, but certain be its restriction that is not subjected to these compounds.Below show a part of instantiation.
Low molecule class hole is injected and is carried material
Macromolecule class hole is injected and is carried material
Inject to carry the property material as electronics, can select arbitrarily to have easily and inject electronics, injected electrons is delivered to the compound of the function of luminescent layer, and consider that the balance of the carrier mobility of itself and hole transporting material selects from negative electrode.As material with electronics injection transportation performance, but Ju Chu oxadiazole derivative, oxazole derivative, thiazole, thiadiazoles derivative, pyrazole derivatives, triazole derivative, pyrrolotriazine derivatives, pyrene derivatives, quinoline, quinoxaline derivatices, fluorenone derivatives, anthracyclinone derivatives, phenanthroline derivative, metal-organic complex etc., but certain be its restriction that is not subjected to these compounds.Below show a part of instantiation.
The layer that the organic compound of organic illuminating element of the present invention forms generally can or be dissolved in the appropriate solvent by vacuum vapour deposition, ionization vapour deposition method, sputtering method, plasma method and form film by known coating process (for example spin-coating method, dip coating, casting, LB method, ink-jet method etc.).Particularly when adopting the coating process film forming, also can form film by the suitable binding resin of combination.
As above-mentioned binding resin, can be from selecting the adhesion resin widely, for example can enumerate Polectron, polycarbonate resin, mylar, poly-arylide resin, polystyrene resin, ABS resin, polybutadiene, polyurethane resin, acrylic resin, methacrylic resin, butyral resin, the polyvinyl acetal resin, polyamide, polyimide resin, polyvinyl resin, polyethersulfone resin, diallyl phthalate, phenolic resin, epoxy resin, the silicone resin, polysulfone resin, urea resin etc., but it is not subjected to the restriction of these resins.In addition, these resins can use separately, perhaps as the copolymer polymer, with mixed with resin more than a kind or 2 kinds.In addition, also can be as required, and with the additive of known plasticiser, antioxidant, ultraviolet absorber etc.
As anode material, be preferably the big as far as possible material of work function, for example can use the metal monomer of gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, tungsten etc., perhaps be the metal oxide of the alloy, tin oxide, zinc oxide, indium oxide, indium tin oxide target (ITO), indium zinc oxide etc. of these metals.In addition, also can use the electric conductive polymer of polyaniline, polypyrrole, polythiophene, polyhenylene thioether etc.These electrode substances can use separately, also can and use multiple above material.In addition, anode can constitute 1 layer, also can constitute multilayer.
On the other hand, as cathode material, be preferably the work function materials with smaller, for example be the metal monomer of lithium, sodium, potassium, calcium, magnesium, aluminium, indium, ruthenium, titanium, manganese, yttrium, silver, lead, tin, chromium etc., perhaps lithium-indium, sodium-potassium, magnesium-Yin, aluminium-lithium, aluminium-magnesium, magnesium-indium etc. can be used as multiple alloy.Also can utilize the metal oxide of indium tin oxide target (ITO) etc.These electrode substances can use separately, also can and use multiple material.In addition, negative electrode can constitute 1 layer, also can constitute multilayer.
In addition, at least one side in preferred anodes and the negative electrode is transparent or semitransparent.
As the used substrate of the present invention, it is not particularly limited, can use the transparent substrate of opaque substrate, glass, quartz, plastic sheets etc. such as substrate that metal substrate, pottery make.In addition, also can be by on substrate, using colour transition filter membrane, iridescent transform filter film, dielectric reflectance coating etc., control color development light.
In addition,, contact with moisture etc. with oxygen, also protective layer or sealant can be set in order to prevent it for the element of making.As protective layer, can enumerate the polymeric membrane of the inorganic material film, fluororesin, Parylene, polyethylene, silicone resin, polystyrene resin etc. of diamond thin, metal oxide, metal nitride etc., also can enumerate light-cured resin etc.In addition, also can pass through cover glass, gas impermeability film, metal etc., element itself be encapsulated by the suitable seal resin.
Embodiment
The present invention will be described in more detail by the following examples, but the present invention is not limited to these embodiment.
The organic illuminating element of structure shown in Figure 3 is made according to method shown below.
On glass substrate as substrate 1, on indium tin oxide target (ITO), make the thick film of 120nm with sputtering method as anode 2, and with it as the transparent conductivity support substrate.After using acetone, isopropyl alcohol (IPA) that it is carried out ultrasonic waves for cleaning in order, boil cleaning, after this carry out drying with IPA.Further use the UV/ ozone clean, it is used as transparent conductivity support substrate.
Adopt the compound shown in the following structural formula as the positivity hole transporting material, it is adjusted into the chloroformic solution that concentration is 0.5 weight %.
This drips of solution is added on the above-mentioned ITO electrode, carries out 10 seconds spin coating with the rotary speed of 500RPM at first, carry out 1 minute spin coating then with the rotary speed of 1000RPM, form film.After this, drying is 10 minutes in 80 vacuum furnace, to remove the solvent in the film fully.The thickness of the hole transporting layer 5 that forms is 50nm.Then, will carry out common evaporation (weight ratio 10: 90) as the above-mentioned exemplary compounds NO.39 of the 1st compound with as the above-mentioned exemplary compounds NO.201 of the 2nd compound, it is the luminescent layer 3 of 20nm that thickness is set.Condition during evaporation is that vacuum degree is 1.0 * 10
-4Pa, film forming speed are 0.2～0.3nm/ second, make film thus.
After this, make bathophenanthroline (BPhen) form the thickness of 40nm by vacuum vapour deposition, as electron supplying layer 6.Condition during evaporation is that vacuum degree is 1.0 * 10
-4Pa, film forming speed are 0.2～0.3nm/ second.
Then, the deposition material that adopts aluminum-copper-lithium alloys (lithium concentration is 1 atom %) to constitute, by forming the metal tunic that thickness is 10nm on the vacuum vapour deposition organic layer formerly, after this by vacuum vapour deposition the thick aluminium film of 150nm is set, the aluminum-copper-lithium alloys film is made electron injection electrode (negative electrode 4), make organic illuminating element thus.In vacuum degree is 1.0 * 10
-4Pa, film forming speed are evaporation film-forming under 1.0～1.2nm/ condition of second.
For the organic EL that makes gained can not become bad owing to adsorption moisture causes element, covering protection glass plate in the air atmosphere of drying, and seal with the crylic acid resin binding agent.
On the element of gained thus, with ITO electrode (anode 2) as anodal, Al-Li electrode (negative electrode 4) as negative pole, applying under the voltage of 3.5V, can be observed glorious degrees is 900cd/m
2, luminous efficiency is the blue-green light that exemplary compounds 39 81m/W, have maximum emission wavelength at the 490nm place is sent.
In addition, by adopting analyzer AC-1 (reason is ground the machine manufacturing) to carry out the mensuration that ionization potential is measured, carried out band gap by the ultraviolet-visible light absorption, the HOMO/LUMO energy level that can estimate exemplary compounds No.39 is-5.58eV/-2.86eV, the HOMO/LUMO energy level of exemplary compounds No.201 is-5.70eV/-2.78eV, hence one can see that, and the 2nd compound is wideer than the band gap of the 1st compound, and the HOMO energy level of the 1st compound is lower than the lumo energy of the 2nd compound than the lumo energy of the HOMO energy level height of the 2nd compound and the 1st compound.
In addition, under nitrogen atmosphere, this element applied 100 hours voltage, and make current density remain on 30mA/cm
2The time, from the initial stage be about 2400cd/m
2After 100 hours, be about 2150cd/m
2, the briliancy deterioration condition is very slight.
＜comparative example 1 〉
Except replace exemplary compounds No.201 with compound (three (oxine) aluminium) shown in following, adopt the mode the same to make element, and carry out same evaluation with embodiment 1 as the 2nd compound.
Applying under the voltage of 3.5V, can be observed glorious degrees is 200cd/m
2, luminous efficiency is green light 31m/W, have maximum emission wavelength at the 510nm place.
In addition, the HOMO/LUMO energy level that estimates three (oxine) aluminium is-5.70eV/-3.01eV.
At this moment, because the lumo energy of the 1st compound is low than the lumo energy of the 2nd compound, therefore supposition is low in the join probability again in the electronics of the 1st compound and hole, and luminous efficiency is low.
＜embodiment 2～5 〉
Except adopting exemplary compounds No.37 as the 1st compound, adopt compound shown in the table 1 as beyond the 2nd compound, adopt the mode the same to make element, and carry out same evaluation with embodiment 1.
Table 1
| Embodiment | The sequence number No. of the exemplary compounds of the 2nd compound | Apply voltage (V) | Briliancy (cd/m 2) | Efficient (lm/W) |
| ??2 | ??101 | ??3.5 | ????750 | ????8 |
| ??3 | ??107 | ??3.5 | ????1400 | ????10 |
| ??4 | ??201 | ??3.5 | ????2100 | ????11 |
| ??5 | ??212 | ??3.5 | ????900 | ????8 |
In any one embodiment, obtain all coming from that exemplary compounds No.37 sends has the green light of maximum emission wavelength at the 510nm place.
And, known in any one embodiment, the band gap of the 2nd compound is wideer than the band gap of the 1st compound (exemplary compounds No.37), and the HOMO energy level of the 1st compound is lower than the lumo energy of the 2nd compound than the lumo energy of the HOMO energy level height of the 2nd compound, the 1st compound.
In addition, under nitrogen atmosphere, the element of embodiment 2 applied 100 hours voltage, and make current density remain on 30mA/cm
2The time, from the initial stage be about 2500cd/m
2After 100 hours, be about 2200cd/m
2, the briliancy deterioration condition is very slight.
＜comparative example 2 〉
Except adopting following compound, adopt the mode the same to make element, and carry out same evaluation with embodiment 2 as the 1st compound.Applying under the voltage of 3.5V, can be observed glorious degrees is 450cd/m
2, luminous efficiency is green emitting 5.0lm/W, have maximum emission wavelength at the 505nm place.
In addition, under nitrogen atmosphere, this element applied 100 hours voltage, and make current density remain on 30mA/cm
2The time, from the initial stage be about 1700cd/m
2After 100 hours, be about 800cd/m
2, the briliancy deterioration condition is very big.
＜embodiment 6～9 〉
Except adopting exemplary compounds No.22 as the 1st compound, adopt compound shown in the table 1 as the 2nd compound, and the common evaporation ratio that makes luminescent layer be 15: 85 (weight ratio) in addition, adopt the mode the same to make element, and carry out same evaluation with embodiment 1.The results are shown in table 2.
Table 2
| Embodiment | The sequence number No. of the exemplary compounds of the 2nd compound | Apply voltage (V) | Briliancy (cd/m 2) | Efficient (lm/W) |
| ??6 | ??101 | ????3.5 | ????350 | ????8 |
| ??7 | ??107 | ????3.5 | ????700 | ????11 |
| ??8 | ??201 | ????3.5 | ????1050 | ????14 |
| ??9 | ??212 | ????3.5 | ????500 | ????10 |
In any one embodiment, obtain all coming from that exemplary compounds No.22 sends has the green light of maximum emission wavelength at the 530nm place.
And, known in any one embodiment, the band gap of the 2nd compound is wideer than the band gap of the 1st compound (exemplary compounds No.22), and the HOMO energy level of the 1st compound is lower than the lumo energy of the 2nd compound than the lumo energy of the HOMO energy level height of the 2nd compound, the 1st compound.
＜embodiment 10～13 〉
Except adopting exemplary compounds No.34 as the 1st compound, adopt compound shown in the table 1 as the 2nd compound, and the common evaporation ratio that makes luminescent layer be 35: 65 (weight ratio) in addition, adopt the mode the same to make element, and carry out same evaluation with embodiment 1.The results are shown in table 3.
Table 3
| Embodiment | The sequence number No. of the exemplary compounds of the 2nd compound | Apply voltage (V) | Briliancy (cd/m 2) | Efficient (lm/W) |
| ??10 | ?101 | ??3.5 | ????1100 | ????10 |
| ??11 | ?107 | ??3.5 | ????2600 | ????15 |
| ??12 | ?201 | ??3.5 | ????3900 | ????17 |
| ??13 | ?212 | ??3.5 | ????1900 | ????12 |
In any one embodiment, obtain all coming from that exemplary compounds No.34 sends has the yellow-green light of maximum emission wavelength at the 535nm place.
And it is known in any one embodiment, the band gap of the 2nd compound is wideer than the band gap of the 1st compound (exemplary compounds No.34), and the HOMO energy level of the 1st compound is lower than the lumo energy of the 2nd compound than the lumo energy of the HOMO energy level height of the 2nd compound, the 1st compound.
＜embodiment 14 〉
Except adopting exemplary compounds No.40 as the 1st compound, adopt exemplary compounds No.202 as the 2nd compound, and the common evaporation ratio that makes luminescent layer be 20: 80 (weight ratio) in addition, adopt the mode the same to make element, and carry out same evaluation with embodiment 1.Applying under the voltage of 3.5V, can be observed glorious degrees is 2000cd/m
2, luminous efficiency is green light 13lm/W, have maximum emission wavelength at the 530nm place, that sent by exemplary compounds No.40.
By ionization potential measure and the ultraviolet-visible light absorption to the mensuration of band gap, the HOMO/LUMO energy level that can estimate exemplary compounds No.40 is-5.51eV/-3.10eV, the HOMO/LUMO energy level of exemplary compounds No.202 is-5.73eV/-2.85eV, hence one can see that, and the 2nd compound is wideer than the band gap of the 1st compound, and the HOMO energy level of the 1st compound is lower than the lumo energy of the 2nd compound than the lumo energy of the HOMO energy level height of the 2nd compound and the 1st compound.
＜embodiment 15 〉
Except adopting exemplary compounds No.48 as the 1st compound, adopt exemplary compounds No.101 as the 2nd compound, and the common evaporation ratio that makes luminescent layer be 5: 95 (weight ratio) in addition, adopt the mode the same to make element, and carry out same evaluation with embodiment 1.Applying under the voltage of 4.0V, can be observed glorious degrees is 500cd/m
2, luminous efficiency is cyan light 4lm/W, have maximum emission wavelength at the 450nm place, that sent by exemplary compounds No.48.
By ionization potential measure and the ultraviolet-visible light absorption to the mensuration of band gap, the HOMO/LUMO energy level that can estimate exemplary compounds No.48 is-5.75eV/-2.85eV, the HOMO/LUMO energy level of exemplary compounds No.101 is-5.81eV/-2.76eV, hence one can see that, and the 2nd compound is wideer than the band gap of the 1st compound, and the HOMO energy level of the 1st compound is lower than the lumo energy of the 2nd compound than the lumo energy of the HOMO energy level height of the 2nd compound and the 1st compound.
＜embodiment 16 〉
Except adopting exemplary compounds No.57 as the 1st compound, adopt exemplary compounds No.201 as the 2nd compound, and the common evaporation ratio that makes luminescent layer be 35: 65 (weight ratio) in addition, adopt the mode the same to make element, and carry out same evaluation with embodiment 1.Applying under the voltage of 3.5V, can be observed glorious degrees is 3100cd/m
2, luminous efficiency is yellow-green light 13lm/W, have maximum emission wavelength at the 540nm place, that sent by exemplary compounds No.57.
By ionization potential measure and the ultraviolet-visible light absorption to the mensuration of band gap, the HOMO/LUMO energy level that can estimate exemplary compounds No.57 is-5.52eV/-3.10eV, the HOMO/LUMO energy level of exemplary compounds No.201 is-5.70eV/-2.78eV, hence one can see that, and the 2nd compound is wideer than the band gap of the 1st compound, and the HOMO energy level of the 1st compound is lower than the lumo energy of the 2nd compound than the lumo energy of the HOMO energy level height of the 2nd compound and the 1st compound.
＜embodiment 17 〉
Except adopting exemplary compounds No.4 as the 1st compound, adopt exemplary compounds No.201 as the 2nd compound, and the common evaporation ratio that makes luminescent layer be 35: 65 (weight ratio) in addition, adopt the mode the same to make element, and carry out same evaluation with embodiment 1.Applying under the voltage of 3.5V, can be observed glorious degrees is 3900cd/m
2, luminous efficiency is green light 18lm/W, have maximum emission wavelength at the 530nm place, that sent by exemplary compounds No.4.
By ionization potential measure and the ultraviolet-visible light absorption to the mensuration of band gap, the HOMO/LUMO energy level that can estimate exemplary compounds No.4 is-5.49eV/-2.99eV, the HOMO/LUMO energy level of exemplary compounds No.201 is-5.70eV/-2.78eV, hence one can see that, and the 2nd compound is wideer than the band gap of the 1st compound, and the HOMO energy level of the 1st compound is lower than the lumo energy of the 2nd compound than the lumo energy of the HOMO energy level height of the 2nd compound and the 1st compound.
In addition, under nitrogen atmosphere, the element of embodiment 17 applied 100 hours voltage, and make current density remain on 10mA/cm
2The time, from the initial stage be about 2000cd/m
2After 100 hours, be about 1800cd/m
2, the briliancy deterioration condition is very little.
＜embodiment 18 〉
Except on electron supplying layer, using 2, beyond 9-two [2-(9,9-dimethyl the fluorenyl)] phenanthroline, adopt the mode the same to make element, and carry out same evaluation with embodiment 17.
Applying under the voltage of 3.5V, can be observed glorious degrees is 3900cd/m
2, luminous efficiency is green light 18lm/W, have maximum emission wavelength at the 530nm place, that sent by exemplary compounds No.4.
And, under nitrogen atmosphere, the element of embodiment 18 applied 100 hours voltage, and make current density remain on 10mA/cm
2The time, from the initial stage be about 2000cd/m
2After 100 hours, be about 1900cd/m
2, the briliancy deterioration condition is very little.
Compare with embodiment 17,, not only can keep the luminous efficiency of equal extent, and can improve the bad situation that becomes that drives by changing electron transport materials.Even in luminescent layer, use other exemplary compounds beyond the present embodiment, can obtain same effect.
＜embodiment 19 〉
Except adopting exemplary compounds No.16 as the 1st compound, adopt exemplary compounds No.201 as the 2nd compound, and the common evaporation ratio that makes luminescent layer be 25: 65 (weight ratio) in addition, adopt the mode the same to make element, and carry out same evaluation with embodiment 1.Applying under the voltage of 3.5V, can be observed glorious degrees is 3300cd/m
2, luminous efficiency is green light 15lm/W, have maximum emission wavelength at the 525nm place, that sent by exemplary compounds No.4.
By ionization potential measure and the ultraviolet-visible light absorption to the mensuration of band gap, the HOMO/LUMO energy level that can estimate exemplary compounds No.16 is-5.48eV/-3.00eV, the HOMO/LUMO energy level of exemplary compounds No.201 is-5.70eV/-2.78eV, hence one can see that, and the 2nd compound is wideer than the band gap of the 1st compound, and the HOMO energy level of the 1st compound is lower than the lumo energy of the 2nd compound than the lumo energy of the HOMO energy level height of the 2nd compound and the 1st compound.
Describe as can be known by exemplifying above execution mode and embodiment, according to the present invention, can provide have high briliancy, the organic illuminating element of high efficiency and ageing stability excellence.
Claims (5)
1. organic illuminating element, it has 1 pair of electrode that anode and negative electrode form at least, and clamping between this 1 pair of electrode comprises the layer of a kind or multiple organic compound,
In comprising the layer of described organic compound, at least 1 layer of light-emitting zone contains the 1st compound shown in the following general formula [1] and has 2nd compound bigger than the 1st compound band gap:
In general formula [1], A represents to comprise the molecular cell of aromatic rings, fused polycycle, heterocycle etc.;
Y
1, Y
2For being selected from replacement or unsubstituted alkyl, aralkyl, aryl and heterocyclic radical, having the group that connects basic divalent substituent, the two can be the same or different; Perhaps, Y
1, Y
2Also can interosculate and form ring; Perhaps, the Y on different anthracene deriveding groups
1And Y
2Can be the same or different;
Z
1Be the heterocyclic radical that is selected from direct key, replacement or unsubstituted arlydene and divalence, the group with the divalent substituent that is connected base, it can be the same or different; Z
2And Z
3For being selected from direct key, replacement or unsubstituted alkylidene, alkenylene, alkynylene, arylmethylene alkyl, arylene and divalent heterocycle, having the group that is connected basic divalent substituent, it can be the same or different;
X
1Be silicyl, the boryl that is selected from hydrogen atom, D atom, halogen atom, replacement or unsubstituted alkyl, thiazolinyl, alkynyl, aralkyl, alkoxyl, sulfenyl, aryl and heterocyclic radical, replacement, the group with the divalent substituent that is connected base, it can be the same or different; X
2For be selected from replace or unsubstituted aryl with heterocyclic radical, have the group that is connected basic divalent substituent, it can be the same or different;
R
1And R
2For being selected from the group of hydrogen atom, D atom, halogen atom, replacement or unsubstituted alkyl, aryl, alkoxyl, amino, it can be the same or different; R
3For being selected from the group of hydrogen atom, D atom, halogen atom, replacement or unsubstituted alkyl, alkoxyl, it can be the same or different;
A is 0～6 integer; B+c+d=6-a; But when a+b is a integer more than 2, during a=0, the X on anthryl
1In, have at least one to comprise hydrogen atom, D atom, halogen atom substituting group in addition.
2. organic illuminating element as claimed in claim 1, described the 1st compound is shown in following general formula [2]:
In general formula (2), Y
3, Y
4For being selected from replacement or unsubstituted alkyl, aralkyl, aryl and heterocyclic radical, having the group that is connected basic divalent substituent, it can be the same or different; In addition, Y
3, Y
4Also can be connected to each other and form ring; In addition, the different anthracenes Y on the base that derives
3, Y
4Can be the same or different;
Z
4Be the heterocyclic radical that is selected from direct key, replacement or unsubstituted arlydene and divalence, the group with the divalent substituent that is connected base, it can be the same or different; Z
5And Z
6For be selected from direct key, replacement or unsubstituted alkylidene, alkenylene, alkynylene, inferior aralkyl, arylene with divalent heterocycle, have the group of divalent substituent that is connected base, it can be the same or different;
X
3Be silicyl, the boryl that is selected from hydrogen atom, D atom, halogen atom, replacement or unsubstituted alkyl, thiazolinyl, alkynyl, aralkyl, alkoxyl and sulfenyl, aryl and heterocyclic radical, replacement, the group with the divalent substituent that is connected base, it can be the same or different; X
4For be selected from replace or unsubstituted aryl with heterocyclic radical, have the group that is connected basic divalent substituent, it can be the same or different;
R
4And R
5For being selected from the group of hydrogen atom, D atom, halogen atom, replacement or unsubstituted alkyl, aryl, alkoxyl, amino, it can be the same or different; R
6For being selected from the group of hydrogen atom, D atom, halogen atom, replacement or unsubstituted alkyl, alkoxyl, it can be the same or different;
E is 0～6 integer; F+g+h=6-e; But when e+f is a integer more than 2, during e=0, the X on anthryl
3In, have at least one to comprise hydrogen atom, D atom, halogen atom substituting group in addition.
3. organic illuminating element as claimed in claim 1, the HOMO energy level of wherein said the 1st compound is than the energy level height of described the 2nd compound, and the lumo energy of described the 1st compound is lower than the lumo energy of described the 2nd compound.
4. organic illuminating element as claimed in claim 1, wherein said the 2nd compound is shown in following general formula [3]:
In general formula [3], R
7, R
8, R
9And R
10Amino, cyano group or the halogen atom of expression hydrogen atom, replacement or unsubstituted alkyl, replacement or unsubstituted aralkyl, replacement or unsubstituted aryl, replacement or unsubstituted heterocyclic, replacement; R
7, R
8, R
9And R
10Can be identical, also can be different; Ar
1And Ar
2Expression replaces or unsubstituted condensed polycyclc aromatic base or expression replacement or unsubstituted fused polycycle heterocyclic radical, Ar
1And Ar
2Can be identical, also can be different.
5. organic illuminating element as claimed in claim 1, wherein said the 2nd compound is shown in following general formula [4]:
In general formula [4], R
11And R
12Amino, cyano group or the halogen atom of expression hydrogen atom, replacement or unsubstituted alkyl, replacement or unsubstituted aralkyl, replacement or unsubstituted aryl, replacement or unsubstituted heterocyclic, replacement; R
11And R
12Can be identical, also can be different; R
13And R
14Expression hydrogen atom, replacement or unsubstituted alkyl, replacement or unsubstituted aralkyl, replacement or unsubstituted aryl, replacement or unsubstituted heterocyclic; R
13And R
14Can be identical, also can be different; Ar
3And Ar
4The expression phenyl ring is replacement or the unsubstituted condensed polycyclc aromatic base more than 3 or represents that phenyl ring is replacement or the unsubstituted fused polycycle heterocyclic radical more than 3, Ar
3And Ar
4Can be identical, also can be different; N represents 1～10 integer.
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| JP2004149953A JP3840235B2 (en) | 2003-06-27 | 2004-05-20 | Organic light emitting device |
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| US (1) | US7491450B2 (en) |
| EP (1) | EP1491610B1 (en) |
| JP (1) | JP3840235B2 (en) |
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| CN100393678C (en) * | 2006-03-17 | 2008-06-11 | 中国科学院长春应用化学研究所 | Series soluble oligomer using 9,10-diacetylenic anthracene as stractural unit and preparing method |
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| CN104752619A (en) * | 2013-12-26 | 2015-07-01 | 东丽先端材料研究开发（中国）有限公司 | Organic light-emitting element |
| CN105849930A (en) * | 2013-12-26 | 2016-08-10 | 东丽株式会社 | Organic light-emitting element |
| CN108129441A (en) * | 2017-12-13 | 2018-06-08 | 南京邮电大学 | A kind of organic laser material of steric hindrance type multi-arm oligomerization fluorenes and preparation method thereof |
| CN113851588A (en) * | 2020-06-28 | 2021-12-28 | 冠能光电材料(深圳)有限责任公司 | Electroluminescent material and application thereof in organic light-emitting device |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE489446T1 (en) | 2010-12-15 |
| DE602004030189D1 (en) | 2011-01-05 |
| EP1491610A2 (en) | 2004-12-29 |
| US7491450B2 (en) | 2009-02-17 |
| US20040265632A1 (en) | 2004-12-30 |
| EP1491610B1 (en) | 2010-11-24 |
| EP1491610A3 (en) | 2006-06-21 |
| JP3840235B2 (en) | 2006-11-01 |
| JP2005038829A (en) | 2005-02-10 |
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